5-((1-ethyl-5-nitro-1H-indol-3-yl)methyl)-2-methoxy-N-(4-nitrophenylsulfonyl)benzamide

ID: ALA5194419

PubChem CID: 168286229

Max Phase: Preclinical

Molecular Formula: C25H22N4O8S

Molecular Weight: 538.54

Names and Identifiers

Canonical SMILES:  CCn1cc(Cc2ccc(OC)c(C(=O)NS(=O)(=O)c3ccc([N+](=O)[O-])cc3)c2)c2cc([N+](=O)[O-])ccc21

Standard InChI:  InChI=1S/C25H22N4O8S/c1-3-27-15-17(21-14-19(29(33)34)7-10-23(21)27)12-16-4-11-24(37-2)22(13-16)25(30)26-38(35,36)20-8-5-18(6-9-20)28(31)32/h4-11,13-15H,3,12H2,1-2H3,(H,26,30)

Standard InChI Key:  YCMHZUIVUZNITL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -3.8977   -1.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712   -1.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712   -2.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1813   -3.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977   -2.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6865   -2.9009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6864   -1.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4728   -0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -0.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4620    0.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328    0.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9165   -0.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898   -1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135    0.0839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464    1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370    1.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    1.4647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    2.2618    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    2.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5679    3.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    3.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    2.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    2.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9401    1.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435    3.1145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270    2.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571    3.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    3.0885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    2.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -3.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6123   -1.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6123   -0.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3270   -1.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  8  7  1  0
  9  8  2  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 14 17  1  0
 17 18  1  0
 13 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 23 28  1  0
 29 26  1  0
 29 30  1  0
 29 31  2  0
 22 32  2  0
 22 33  2  0
  7 34  1  0
 34 35  1  0
 36  1  1  0
 36 37  1  0
 36 38  2  0
M  CHG  4  29   1  30  -1  36   1  37  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5194419

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 538.54

Molecular Weight (Monoisotopic): 538.1158

AlogP: 4.20

#Rotatable Bonds: 9

Polar Surface Area: 163.68

Molecular Species: ACID

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.18

CX Basic pKa: ┄

CX LogP: 4.92

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -1.18

References

1. Howard KC, Garneau-Tsodikova S..  (2022)  Selective Inhibition of the Periodontal Pathogen Porphyromonas gingivalis by Third-Generation Zafirlukast Derivatives.,  65  (21.0): [PMID:36273428] [10.1021/acs.jmedchem.2c01471]

Source

Source(1):

• Scientific Literature